Abstract
A sensitive and specific high performance liquid chromatography coupled with fluorescent detection (HPLC-FL) and tandem mass spectrometry detection (HPLC-MS/MS) methods for separation and determination of carvedilol (CAR) enantiomers and 5′-hydroxyphenyl carvedilol (5′-HCAR) enantiomers has been developed and validated. The analysed compounds were extracted from human urine by solid phase extraction. Good enantioseparation of the studied enantiomers was achieved on CHIRALCEL® OD-RH column using 0.05% trifluoroacetic acid and 0.05% diethylamine in water and acetonitrile in a gradient elution. The mass spectrometric data were acquired using the multiple reaction monitoring mode by positive electrospray ionisation. The method was validated over the concentration range from 25.0 ng mL−1 to 200 ng mL−1 for the analysed compounds. The limit of quantification varied from 14.2 ng mL−1 to 24.2 ng mL−1. Both the repeatability and inter-day precisions were below 10.0%, and the accuracy varied from −13.2% to 3.77%. The extraction recoveries ranged from 79.2% to 108%. The present paper reports the method for the simultaneous determination of CAR enantiomers and their metabolite enantiomers (5′-HCAR) in human urine samples. This newly developed method was successfully used to analyse the aforementioned analytes in human urine samples obtained from patients suffering from cardiovascular disease.
Similar content being viewed by others
References
W.H. Frishman, N. Engel. J. Med. 339, 1759 (1998)
W. Bartsch, G. Sponer, K. Strein, B. Müller-Beckmann, L. Kling, E. Böhm, U. Martin, H.O. Borbe, Eur. J. Clin. Pharmacol. 38, S104 (1990)
G.L. Erny, A. Cifuentes, J. Pharm. Biomed. Anal. 40, 509 (2006)
K. Stoschitzky, G. Koshucharova, P. Lercher, R. Maier, A. Sakotnik, W. Klein, P.M. Liebmann, W. Lindner, Chirality 13, 342 (2001)
K. Stoschitzky, G. Koshucharova, R. Zweiker, P. Lercher, R. Maier, W. Klein, S. Zitta, L. Gruber, G. Lamprecht, W. Lindner, Cardiovasc. Drugs Ther. 16, 133 (2002)
A. Medvedovici, F. Albu, C. Georgita, D.I. Sora, T. Galaon, S. Udrescu, V. David, J. Chromatogr. B 850, 327 (2007)
T.W.B. Gehr, D.M. Tenero, D.A. Boyle, Y. Qian, D.A. Sica, N.H. Shusterman, Eur. J. Clin. Pharmacol. 55, 269 (1999)
M. Zakrzewski-Jakubiak, S. de Denus, M.-H. Leblanc, M. White, J. Turgeon, J. Pharm. Biomed. Anal. 52, 636 (2010)
M. Saito, J. Kawana, T. Ohno, M. Kaneko, K. Mihara, K. Hanada, R. Sugita, N. Okada, S. Oosato, M. Nagayama, T. Sumiyoshi, H. Ogata, J. Chromatogr. B 843, 73 (2006)
R.G. Peccinini, V.F. Ximenes, E.J. Cesarino, V.L. Lanchote, Biopharm. Drug Dispos. 29, 280 (2008)
G. Larnprecht, L. Gruber, K. Stoschitzky, W. Lindner, Chromatographia 56, S–25 (2002)
L. Clohs, K.M. McErlane, J. Pharm. Biomed. Anal. 31, 407 (2003)
E. Yang, S. Wang, J. Kratz, M.J. Cyronak, J. Pharm. Biomed. Anal. 36, 609 (2004)
E.J. Eisenberg, W.R. Patterson, G.C. Kahn, J. Chromatogr. B 493, 105 (1989)
H. Spahn, W. Henke, P. Langguth, J. Schloos, E. Mutschler, Arch. Pharm. (Weinheim) 323, 465 (1990)
E. Stahl, E. Mutschler, U. Baumgartner, H. Spahn-Langguth, Arch. Pharm. (Weinheim) 326, 529 (1993)
G. Neugebauer, W. Akpan, B. Kaufmann, K. Reiff, Eur. J. Clin. Pharmacol. 38, S108 (1990)
I. Baranowska, P. Markowski, J. Baranowski, Anal. Sci. 25, 1307 (2009)
M. Machida, M. Watanabe, S. Takechi, S. Kakinoki, A. Nomura, J. Chromatogr. B 798, 187 (2003)
A. Zarghi, S.M. Foroutan, A. Shafaati, A. Khoddam, J. Pharm. Biomed. Anal. 44, 250 (2007)
N. Hokama, N. Hobara, H. Kameya, S. Ohshiro, M. Sakanashi, J. Chromatogr. B 732, 233 (1999)
R. Rathod, P.Ch. Prasad, S. Rani, M. Nivsarkar, H. Padh, J. Chromatogr. B 857, 219 (2007)
P. Ptáček, J. Macek, J. Klíma, J. Chromatogr. B 798, 405 (2003)
M.P. McIntosh, B.J. Carlson, K.S. Schorno, R.A. Rajewski, J. Chromatogr. B 852, 665 (2007)
D.W. Jeong, Y.H. Kim, H.Y. Ji, Y.S. Youn, K.Ch. Lee, H.S. Lee, J. Pharm. Biomed. Anal. 44, 547 (2007)
G. Lamprecht, K. Stoschitzky, Chromatographia 59, 551 (2004)
F. Behn, S. Läer, T.S. Mir, H. Scholz, Chromatographia 53, 641 (2001)
H.H. Maurer, O. Tenberken, C. Kratzsch, A.A. Weber, F.T. Peters, J. Chromatogr. A 1058, 169 (2004)
L. Kristoffersen, E.L. Øiestad, M.S. Opdal, M. Krogh, E. Lundanes, A.S. Christophersen, J. Chromatogr. B 850, 147 (2007)
N.C. do Carmo Borges, G.D. Mendes, D. de Oliveira Silva, V.M. Rezende, R.E. Barrientos-Astigarraga, G.D. Nucci, J. Chromatogr. B 822, 253 (2005)
S.W. Myung, Ch.H. Jo, J. Chromatogr. B 822, 70 (2005)
S. Magiera, C. Uhlschmied, M. Rainer, Ch.W. Huck, I. Baranowska, G.K. Bonn, J. Pharm. Biomed. Anal. 56, 93 (2011)
F. Behn, S. Michels, S. Läer, G. Blaschke, J. Chromatogr. B 755, 111 (2001)
I. Baranowska, S. Magiera, J. Baranowski, J. Chromatogr. B 879, 615 (2011)
P. Konieczka, Crit. Rev. Anal. Chem. 37, 173 (2007)
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Magiera, S., Adolf, W. & Baranowska, I. Simultaneous chiral separation and determination of carvedilol and 5′-hydroxyphenyl carvedilol enantiomers from human urine by high performance liquid chromatography coupled with fluorescent detection. cent.eur.j.chem. 11, 2076–2087 (2013). https://doi.org/10.2478/s11532-013-0329-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11532-013-0329-x